EP1188799A1 - Mischungen von Dispersionsazofarbstoffen - Google Patents

Mischungen von Dispersionsazofarbstoffen Download PDF

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Publication number
EP1188799A1
EP1188799A1 EP01121526A EP01121526A EP1188799A1 EP 1188799 A1 EP1188799 A1 EP 1188799A1 EP 01121526 A EP01121526 A EP 01121526A EP 01121526 A EP01121526 A EP 01121526A EP 1188799 A1 EP1188799 A1 EP 1188799A1
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EP
European Patent Office
Prior art keywords
dye
formula
alkyl
chlorine
bromine
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Granted
Application number
EP01121526A
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English (en)
French (fr)
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EP1188799B1 (de
Inventor
David Brierley
Ian Weddell
David Newton
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Dystar Colours Distribution GmbH
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Dystar Textilfarben GmbH and Co Deutschland KG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • This invention relates to mixtures of disperse azo dyes.
  • a known azo dye is C.I. Disperse Orange 37 of the formula
  • This dye is disclosed, for example, in CH-A-0406481. Commercially, the dye has been mixed with other dyes to give different shades. However, this dye has been found to act as a skin irritant.
  • BE-A-0592096 also discloses mixtures of dyes of the above formula (d) in which, specifically n D is zero, m D is 1, Y D is NHCOCH 3 and R D 2 is acyloxyalkyl with dyes of the formula (e) wherein
  • the present invention provides a dye mixture comprising at least
  • Alkyl groups may be straight-chained or branched and be for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. butyl or tert.-butyl. This applies as well to alkyl groups in acyloxyalkyl, alkoxy and aralkyl residues.
  • Acyl in acyloxyalkyl is preferably COY wherein Y is C 1-4 alkyl.
  • Aryl is preferably phenyl and naphthyl.
  • Aralkyl is preferably benzyl and phenethyl.
  • the dye of the formula (I) has the formula in which each of X and X 1 independently is chlorine or bromine and R 2 is n-butyl or cyanoethyl, and the mixture additionally contains a dye of the formula (II), given and defined above and optionally a dye of the formula (III), also given and defined above.
  • an especially preferred dye of the formula (I) 1 has the formula (1)
  • Such a dye does not cause irritation to the skin and lends to the mixture excellent heat fastness.
  • a preferred dye of the formula (II) in the mixture has the formula (II) 1 in which X 2 is chlorine or bromine and R 7 is methoxy or ethoxy.
  • a dye mixture of dye components of the respective formulae (I) 1 and (II) 1 preferably contains from 15-75% inclusive of the dye of the formula (I) 1 and from 25-85% inclusive of the dye of the formula (II) 1 , more preferably from 30-60% inclusive of the dye of the formula (I) 1 and from 40-70% inclusive of the dye of the formula (II) 1 , by weight of the weight of the mixture of dyes of the formulae (I) 1 and (II) 1 .
  • this dye component when, in a dye mixture containing dye components of the formula (II) 1 a dye of the formula (III) is additionally present, this dye component preferably has the formula (III) 1 in which X 3 is chlorine or bromine, Y is methyl or ethyl and each of R 9 and R 10 independently is ethyl or allyl.
  • the dye of the formula (II) is preferably a dye (II) 2 in which X 2 is chlorine, each of R 4 and R 5 independently is ethyl, allyl or acetoxyethyl, R 6 is the group NHCOY (in which Y is methyl or ethyl) and R 7 is C 1-6 alkoxy.
  • R 1 is absent, R 2 is n-butyl, R 3 is cyanoethyl and each of X and X 1 is chlorine; in the formula (II), X 2 is bromine, R 6 is the group NHCOY (in which Y is methyl), R 7 is methoxy and each of R 4 and R 5 is allyl; and, in the formula (III) 1 , X 4 is bromine, R 8 is the group NHCOY (in which Y is methyl) and each of R 9 and R 10 is ethyl.
  • a dye mixture containing each of dye components of the respective formulae (I) 1 , (II) and (III) 1 preferably contains, by weight of the weight of the mixture of dyes of the formulae (I) 1 , (II) and (III) 1 ,
  • R 1 is C 1-4 alkyl, more preferably methyl.
  • dyes (I) 2 are referred to below as dyes (I) 2 .
  • a preferred such dye has the formula (2)
  • Such a dye provides especially high colour strength to dye mixtures embodying the invention, especially mixtures which are black in colour.
  • a preferred dye of the formula (II) in the mixture has the formula in which X 2 is chlorine or bromine and R 7 is methoxy or ethoxy.
  • a dye mixture of dye components of the respective formulae (I) 2 and (II) 1 preferably contains from 15-75% inclusive of the dye of the formula (I) 2 and from 25-85% inclusive of the dye of the formula (II) 1 , more preferably from 30-60% inclusive of the dye of the formula (I) 2 , and from 40-70% inclusive of the dye of the formula (II) 1 , by weight of the weight of the mixture of the dyes of formulae (I) 2 and (II) 1 .
  • this dye component when, in a dye mixture containing dye components of the formula (I) 2 and (II) 1 , a dye of the formula (III) is additionally present, this dye component preferably has the formula (III) 2 wherein X 3 is chlorine or bromine and each of R 9 and R 10 independently is ethyl or allyl.
  • the dye of the formula (II) is preferably a dye (II) 2 in which X 2 is chlorine, each of R 4 and R 5 independently ethyl, allyl or acetoxyethyl, R 6 is the group NHCOY (in which Y is methyl or ethyl) and R 7 is C 1-6 alkoxy.
  • each of X and X 1 is chlorine, R 1 is methyl, R 2 is ethyl and R 3 is cyanoethyl; in the formula (II) 2 , X 2 is chloro, each of R 4 and R 5 is allyl, R 6 is the group NHCOY (in which Y is methyl) and R 7 is methoxy; and in the formula (III) 2 , X 3 is chloro and each of R 8 and R 9 is ethyl.
  • a dye mixture containing each of dye components of the respective formula (I) 2 , (II) 2 and (III) 2 preferably contains, by weight of the weight of the mixture of the dyes of the formulae (I) 2 , (II) 2 and (III) 2 ,
  • the dye of the formula (I) has the formula in which each of X and X 1 independently is chlorine or bromine and R 2 is n-butyl or cyanomethyl and the mixture additionally contains a dye of the formula (IV), given and defined above.
  • an especially preferred dye of the formula (I) 1 has the formula
  • Such dye mixtures containing dye components of the formulae (I) and (IV) have particularly good build-up characteristics.
  • each of X and X 1 is chlorine, R 1 is absent, R 2 is n-butyl, and R 3 is cyanoethyl; and, in the formula (IV), R 11 is hydrogen, R 12 is cyano, R 13 is acetoxy and each of m and n is 2.
  • a dye mixture containing each of dye components of the respective formulae (I) 1 and (IV) preferably contains from 10-90% inclusive of the dye of the formula (I) 1 and from 10-90% inclusive of the dye of the formula (IV), by weight of the weight of the mixture of dyes of the formulae (I) 1 and (IV) and more preferably from 25-75% inclusive of the dye of the formula (I) 1 and from 25-75% inclusive of the dye of the formula (IV).
  • All dyes of the formulae (I) - (IV) can be prepared in a conventional manner by diazotising and coupling.
  • dyes of the formula (I) may be prepared by diazotising an amine of the formula (V) wherein each of X and X 1 independently is a chlorine or bromine atom, and coupling the diazotised amine to a coupling component of the formula (VI) wherein each of R 1 , R 2 and R 3 is as defined above.
  • Dyes of the formula (II) may be prepared by diazotising an amine of the formula (VII) wherein X 2 is absent or is chlorine or bromine, and coupling the diazotised amine to a coupling component of the formula (VIII) wherein each of R 4 , R 5 , R 6 and R 7 is as defined above.
  • Dyes of the formula (III) may be prepared by diazotising an amine of the formula (IX) wherein X 3 is absent or is chlorine or bromine, and coupling the diazotised amine to a coupling component of the formula (X) wherein each of R 8 , R 9 and R 10 is as defined above.
  • Dyes of the formula (IV) may be prepared by diazotising an amine of the formula (XI) and coupling the diazotised amine to a coupling component of the formula (XII) wherein each of R 11 , R 12 , R 13 , m and n is as defined above.
  • the diazotisation is carried out using a diazotising agent, which is preferably nitrosyl sulphuric acid, optionally diluted with glacial acetic acid or a phosphoric/acetic acid mixture and preferably at a temperature of 0-10°C, more preferably 0-5°C and preferably at a pH ⁇ 1 (say 0.5) up to 7, more preferably 0.5-1, followed by a subsequent increase in pH to 3-4 to isolate the dye.
  • a diazotising agent which is preferably nitrosyl sulphuric acid, optionally diluted with glacial acetic acid or a phosphoric/acetic acid mixture and preferably at a temperature of 0-10°C, more preferably 0-5°C and preferably at a pH ⁇ 1 (say 0.5) up to 7, more preferably 0.5-1, followed by a subsequent increase in pH to 3-4 to isolate the dye.
  • a mixture embodying the invention of (1) at least one dye of the formula (I) (Component A), at least one dye of the formula (II) (Component B) and optionally at least one dye of the formula (III) or (2) at least one dye of formula (I) (Component A) and at least one dye of the formula (IV) (Component D) may additionally comprise at least one other dye (Component E), especially a yellow, greenish yellow, orange, red or brown dye capable of producing a navy or black shade.
  • such other dyes are present in an amount by weight of up to (but no more than) 10%, more preferably 2-6%, of the total colour.
  • a greenish yellow dye which may be present in an amount of up to 10%, more preferably 2-6%, by weight of total dye colour and which, typically, may be 5-(2'-nitro)phenylazo-6-hydroxy-4-methyl-3-cyano-N-ethyl pyrid-2-one or 5-(2',3'-dichloro)phenylazo-6-hydroxy-4-methyl-3-cyano-N-methylpyrid-2-one.
  • Mixtures embodying the invention can be prepared, for example, by mixing the dye components in the required amounts. Suitable mixing methods include
  • the dyes are dissolved in a hot solvent, for example, by placing the dyes in a suitable solvent and heating up to the reflux temperature of the solvent until the dyes are dissolved, thereafter filtering to provide a solution, and then allowing the solution to cool and crystals to form.
  • suitable solvents for this process are organic solvents such as aromatic hydrocarbons, chlorinated hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons, alcohols, amides, sulphoxides, esters, ketones and ethers.
  • organic solvents are toluene, ethyl cellosolve, acetone, chlorobenzene, pyridine, dimethyl formamide, dimethylsulphoxide, ethyl acetate, benzene, tetrahydrofuran and cyclohexane.
  • Co-crystallisation is generally unsuitable for mixtures containing more than two components.
  • Mixtures embodying the invention provide especially useful disperse dyes valuable for colouring synthetic textile materials and fibre blends thereof by exhaust dyeing, padding or printing, and may be formed into dispersions for this purpose. They may also be used in, for example, ink jet printing of textiles and non-textiles, dye diffusion, thermal transfer printing and in the colouration of plastics.
  • a particular aspect of the invention provides a composition
  • a composition comprising a mixture of (1) dyes (I), (II) and optionally (III) or (2) dyes (I) and (IV), and optionally at least one other disperse dye and, additionally, optionally at least one further ingredient conventionally used in colouring applications such as a dispersing agent, surfactant or wetting agent.
  • the composition typically comprises from 1 % to 65%, preferably 10 to 60%, more preferably 20 to 55%, of the total dye mixture in a liquid, preferably an aqueous, or solid medium.
  • Liquid compositions are preferably adjusted to pH 2 to 7, more preferably pH 4 to 6.
  • dispersing agent examples include lignosulphonates, naphthalene sulphonic acid/formaldehyde condensates and phenol/cresol/sulphanilic acid/formaldehyde condensates
  • typical examples of wetting agent are alkyl aryl ethoxylates which may be sulphonated or phosphated and typical example of other ingredients which may be present are inorganic salts, de-foamers such as mineral oil or nonanol, organic liquids and buffers.
  • Dispersing agents may be present at from 10% to 200% on the weight of the dye mixtures.
  • Wetting agents may be used at from 0% to 20% on the weight of the dye mixtures.
  • compositions may be prepared by bead milling the dye mixture with glass beads or sand in an aqueous medium.
  • the compositions may have further additions of dispersing agents, fillers and other surfactants and may be dried, by a technique such as spray drying, to give a solid composition comprising from 5% to 65% of dyestuff.
  • the invention provides a process for colouring a synthetic textile material or fibre blend thereof which comprises applying to the synthetic textile material or fibre blend a mixture comprising (1) at least one dye of the formula (I), at least one dye of the formula (II) and optionally at least one dye of the formula (III) or (2) at least one dye of the formula (I) and at least one dye of the formula (IV).
  • the synthetic textile material may be selected from aromatic polyester, especially polyethylene terephthalate, polyamide, especially polyhexamethylene adipamide, secondary cellulose acetate, cellulose triacetate, and natural textile materials, especially cellulosic materials and wool.
  • An especially preferred textile material is an aromatic polyester or fibre blend thereof with fibres of any of the above mentioned textile materials.
  • Especially preferred fibre blends include those of polyester-cellulose, such as polyester-cotton, and polyester-wool.
  • the textile materials or blends thereof may be in the form of filaments, loose fibres, yarn or woven or knitted fabrics.
  • mixtures of dyes of formulae (I), (II) and (III) or (I) and (IV), optionally in conjunction with other disperse dyes may be applied to the synthetic textile materials or fibre blends by processes which are conventionally employed in applying disperse dyes to such materials and fibre blends.
  • Suitable process conditions may be selected from the following
  • the dye mixture is applied as a dispersion comprising from 0.001% to 6, preferably from 0.005 to 4%, of the dye mixture in an aqueous medium.
  • the dye mixtures may be applied to synthetic textile materials and fibre blends by ink-jet printing, the substrates optionally having been pre-treated to aid printing.
  • the application medium may comprise water and a water-soluble organic solvent, preferably in a weight ratio of 1:99 to 99:1, more preferably 1:95 to 50:50 and especially in the range 10:90 to 40:60.
  • the water-soluble organic solvent preferably comprises a C 1-4 -alkanol, especially methanol or ethanol, a ketone, especially acetone or methyl ethyl ketone, 2-pyrrolidone or N-methylpyrrolidone, a glycol, especially ethylene glycol, propylene glycol, trimethylene glycol, butane-2,3-diol, thiodiglycol or diethylene glycol, a glycol ether, especially ethylene glycol monomethyl ether, propylene glycol monomethyl ether or diethylene glycol monomethyl ether, urea, a sulphone, especially bis-(2-hydroxyethyl) sulphone or mixtures thereof.
  • a C 1-4 -alkanol especially methanol or ethanol, a ketone, especially acetone or methyl ethyl ketone, 2-pyrrolidone or N-methylpyrrolidone
  • a glycol especially ethylene glycol, propylene glyco
  • the dye mixtures may also be applied to textile materials using supercritical carbon dioxide, in which case the dye formulating agents may optionally be omitted.
  • 2,6-dichloro-4-nitroaniline (0.01m) was dissolved in a mixture of 43 parts acetic acid and 7 parts propionic acid, cooled to 0°C and diazotised by adding 3.0ml of a 40% solution of nitrosyl sulphuric acid in sulphuric acid.
  • the diazo solution was added to a solution of N-butyl-N-(2'-cyanoethyl) aniline (0.01m) in ice/water containing 50ml of acetic acid and 5.0g of sulphamic acid.
  • the coupling reaction mixture was stirred for 1 hour at 0-5°C then allowed to come to room temperature overnight.
  • the product was filtered off, washed with water and dried at 50°C.
  • 2,6-dichloro-4-nitroaniline (0.01m) was dissolved in a mixture of 43 parts acetic acid and 7 parts propionic acid, cooled to 0°C and diazotised by adding 3.0ml of a 40% solution of nitrosyl sulphuric acid in sulphuric acid.
  • the diazo solution was added to a solution of N-ethyl-N(2'-cyanoethyl)-3-toluidine (0.01m) in ice/water containing 50ml of acetic acid and 5.0g of sulphamic acid..
  • the coupling reaction mixture was stirred for 1 hour at 0-5°C then allowed to come to room temperature overnight.
  • 2,4-dinitro-6-chloroaniline (0.12m) was powdered in a mortar and added over 30 minutes to a mixture of nitrosyl sulphuric acid (0.12m) in sulphuric acid (0.7m) while maintaining the temperature at 20-25°C by external cooling. The reaction mixture was stirred for a further 1 hour to complete the diazotisation. 3-N,N-diethyl-4-methoxyacetanilide (0.1m) was dissolved in ice/water (2000ml) containing sulphuric acid (0.10m) and sulphamic acid (5.0g).
  • 2,4-dinitro-6-chloroaniline (0.10m) was dissolved in a mixture of 215 parts acetic acid and 35 parts propionic acid, cooled to 0°C and diazotised by adding 22ml of a 40% solution of nitrosyl sulphuric acid in sulphuric acid. The diazotisation reaction mixture was stirred for 1 hour at 5-10°C. The resulting diazo solution was added slowly to a mixture of 3-N,N-diethyl-acetanilide (0.1m) dissolved in ice/water (3000ml) containing 50ml acetic acid, 5.0g sulphamic acid and 80g of sodium acetate.
  • the coupling reaction mixture was stirred for 1 hour at 0-5°C, then allowed to come to room temperature overnight.
  • the product was filtered off and washed well with 50% aqueous acetone.
  • the press cake was dried at 50°C to give 35.68 of dry solid.
  • the dye was extracted into 500ml of hot ethyl acetate, then allowed to crystallise overnight.
  • the filtered solid was washed first with ethyl acetate then hexane to give 21.6g of a violet dye Component (4) within the formula (III):
  • 2,4-dinitro-6-bromoaniline (0.12m) was powdered in a mortar and added over 30 minutes to a mixture of nitrosyl sulphuric acid (0.12m) in sulphuric acid (0.7m) while maintaining the temperature at 20-25°C by external cooling. The reaction mixture was stirred at this temperature for a further 1 hour to complete the diazotisation.
  • 3-N,N-diethyl 4-methoxyacetanilide (0.1m) was dissolved in ice/water (2000ml) containing sulphuric acid (0.1m) and sulphamic acid (5.0g).
  • 2,4-dinitro-6-bromoaniline (0.12m) was powdered in a mortar and added over 30 minutes to a mixture of nitrosyl sulphuric acid (0.12m) in sulphuric acid (0.7m) while maintaining the temperature at 20-25°C by external cooling.
  • the reaction mixture was stirred for a further 1 hour to complete the diazotisation.
  • the diazo solution was added slowly to a mixture of 3-N,N-diethylacetanilide (0.1m) dissolved in ice/water (2000ml) containing sulphuric acid (0.1m) and sulphamic acid (5.0g).
  • 2,4-dinitro-6-bromoaniline (0.10m) was dissolved in a mixture of 215 parts acetic acid and 35 parts propionic acid, cooled to 0°C and diazotised by adding 20ml of a 40% solution of nitrosyl sulphuric acid in sulphuric acid. The diazotisation reaction mixture was stirred for 1 hour at 5-10°C.
  • 3-N,N-diallyl-4-methoxyacetanilide (0.1m) was dissolved in ice/water (2000ml) containing acetic acid (50ml), sulphamic acid (5.0g) and sodium acetate (40g).
  • the pH of the coupling reaction mixture was adjusted to 4.0 by adding 100ml of a 40%w/v solution of sodium acetate in water.
  • the coupling reaction mixture was stirred for 2 hours at 0-5°C then the product was filtered off, washed with 50% aqueous acetone and dried.
  • the dry product was extracted into 750ml hot ethyl acetate, then allowed to cool overnight.
  • the resulting product was filtered off, washed with ethyl acetate then hexane and dried to yield 36.47g of a pure blue dye Component (7) within the formula (II):
  • 2,4-dinitro-6-chloroaniline (0.10m) was dissolved in a mixture of 215 parts acetic acid and 35 parts propionic acid, cooled to 0°C and diazotised by adding 22ml of a 40% solution of nitrosyl sulphuric acid in sulphuric acid. The diazotisation reaction mixture was stirred for 1 hour at 5-10°C.
  • 3-N,N-diallyl-4-methoxyacetanilide (0.1m) was dissolved in ice/water (3000ml) containing acetic acid (50ml), sulphamic acid (5.0g) and sodium acetate (80g).
  • the same dispersion was standardised to a solid brand containing 55% of the mixture and 45% dispersing agent, by the addition of a temperature stable dispersing agent and drying to either a grain or powder form in a spray dryer.
  • This product is especially suitable for the exhaust dyeing of polyester, polyester/cellulose and polyester/wool blends and can also be used for continuous dyeing and direct printing.
  • a dyebath for the exhaust dyeing of polyester in piece form was prepared by adding 10 mis of an aqueous dispersion of the solid brand (1g dye in 100 mis water at 40-50°C) to 48.8 mis of de-ionised water and 1.2 mis of buffer solution. To this dyebath was added a 5g piece of polyester and the whole was held for 30 minutes at 130°C in a Werner Mathis Labomat high temperature dyeing machine. After rinsing with water and a reduction clearing treatment, the material was dyed to an ISO light black shade.
  • This dispersion was standardised to a solid brand containing 55% of the mixture and 45% dispersing agent, by the addition of a temperature stable dispersing agent and drying to either a grain or powder form in a spray dryer.
  • This product is especially suitable for the exhaust dyeing of polyester, polyester/cellulose and polyester/wool blends and can also be used for continuous dyeing and direct printing.
  • a dyebath for the exhaust dyeing of polyester in piece form was prepared by adding 10 mis of an aqueous dispersion of the solid brand (1g dye in 100 mis water at 40-50°C) to 48.8 mis of de-ionised water and 1.2 mis of buffer solution. To this dyebath was added a 5g piece of polyester and the whole was held for 30 minutes at 130°C in a Werner Mathis Labomat high temperature dyeing machine. After rinsing with water and a reduction clearing treatment, the material was dyed to an ISO light black shade.
  • This dispersion was standardised to a solid brand containing 50% of the mixture and 50% dispersing agent, by the addition of a temperature stable dispersing agent and drying to either a grain or powder form in a spray dryer.
  • This product is especially suitable for the exhaust dyeing of polyester, polyester/cellulose and polyester/wool blends and can also be used for continuous dyeing and direct printing.
  • a dyebath for the exhaust dyeing of polyester in piece form was prepared by adding 3.75 mis of an aqueous dispersion of the solid brand (1g dye in 100 mis water at 40-50°C) to 56.25 mis of de-ionised water and 1.2 mls of buffer solution.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Paper (AREA)
EP01121526A 2000-09-15 2001-09-08 Mischungen von Dispersionsazofarbstoffen Expired - Lifetime EP1188799B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0022697.7A GB0022697D0 (en) 2000-09-15 2000-09-15 Azo disperse dye mixtures
GB0022697 2000-09-15

Publications (2)

Publication Number Publication Date
EP1188799A1 true EP1188799A1 (de) 2002-03-20
EP1188799B1 EP1188799B1 (de) 2012-11-14

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EP01121526A Expired - Lifetime EP1188799B1 (de) 2000-09-15 2001-09-08 Mischungen von Dispersionsazofarbstoffen

Country Status (9)

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US (1) US6682573B2 (de)
EP (1) EP1188799B1 (de)
JP (1) JP4707897B2 (de)
KR (1) KR20020021770A (de)
CN (1) CN1245457C (de)
ES (1) ES2395018T3 (de)
GB (1) GB0022697D0 (de)
PT (1) PT1188799E (de)
TW (1) TWI301502B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7118604B2 (en) 2002-07-29 2006-10-10 Dystar Textilfarben Gmbh & Co. Deutschland Kg Non azo disperse dye mixtures
WO2015193481A3 (en) * 2014-06-20 2016-03-17 Amazon Technologies, Inc. Dye compound, fluid carrier and electrowetting apparatus

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TWI222442B (en) * 2000-12-13 2004-10-21 Aventis Cropscience Gmbh Process for the preparation of 4-haloalkylnicotinonitriles
EP1834031B1 (de) * 2004-11-04 2011-03-02 Feyecon B.V. Verfahren zum färben eines substrats mit einem reaktivfarbstoff in überkritischem oder nahezu überkritischem kohlenstoffdioxid
CN1317339C (zh) * 2005-09-16 2007-05-23 浙江闰土股份有限公司 一种用于印染聚酯材料的组合分散染料
CN100343341C (zh) * 2005-09-28 2007-10-17 杭州吉华化工有限公司 分散染料混合物及其染料制品
CN100558821C (zh) * 2006-07-12 2009-11-11 浙江龙盛集团股份有限公司 一种复合分散染料
CN100503740C (zh) * 2007-01-05 2009-06-24 浙江龙盛染料化工有限公司 一种分散黑染料组合物
CN100503739C (zh) * 2007-01-05 2009-06-24 浙江龙盛染料化工有限公司 一种分散红玉染料组合物
CN100528974C (zh) * 2007-06-18 2009-08-19 浙江闰土股份有限公司 一种复合型拔染印花分散染料
DE102008054531A1 (de) * 2008-12-11 2010-06-17 Dystar Textilfarben Gmbh & Co. Deutschland Kg Mischungen von Dispersionsfarbstoffen
DE102011008683A1 (de) * 2011-01-15 2012-07-19 Dystar Colours Distribution Gmbh Dispersionsfarbstoffmischungen, ihre Herstellung und Verwendung
CN102516811B (zh) * 2011-10-31 2014-07-09 浙江龙盛集团股份有限公司 一种分散黑染料组合物
CN102516812B (zh) * 2011-11-14 2014-03-19 浙江闰土股份有限公司 复合蓝色染料组合物、复合分散蓝染料及其制备方法
CN102604426A (zh) * 2012-01-20 2012-07-25 江苏之江化工有限公司 一种复配型分散黑偶氮染料
CN103275512A (zh) * 2013-05-28 2013-09-04 江苏之江化工有限公司 蓝色单偶氮染料
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CN105086509B (zh) * 2014-08-13 2017-10-03 东华大学 一种可交联活性分散染料化合物及其制备和应用
CN104530751B (zh) * 2014-10-08 2017-06-13 浙江龙盛集团股份有限公司 一种分散红玉染料组合物
CN106752062B (zh) * 2016-12-27 2019-01-29 浙江劲光实业股份有限公司 一种分散蓝染料的制备方法
CN109181358A (zh) * 2018-08-17 2019-01-11 大连傲视化学有限公司 一种分散紫染料化合物在制备分散黑染料混合物中的应用
CN115244139A (zh) * 2020-03-17 2022-10-25 国立大学法人福井大学 用于使用超临界二氧化碳进行染色的染料

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KR20020021770A (ko) 2002-03-22
US20020040510A1 (en) 2002-04-11
PT1188799E (pt) 2013-01-28
GB0022697D0 (en) 2000-11-01
CN1245457C (zh) 2006-03-15
ES2395018T3 (es) 2013-02-07
US6682573B2 (en) 2004-01-27
TWI301502B (en) 2008-10-01
JP4707897B2 (ja) 2011-06-22
JP2002188020A (ja) 2002-07-05
CN1344763A (zh) 2002-04-17
EP1188799B1 (de) 2012-11-14

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